Intermediately formed endocyclic linearly conjugated dienolates, such as (II), react with Michael acceptors to give the corresponding bicyclo(2.2.2)octenes, which lead to C13 degradation products of carotenoids, e.g.(XV) and (XVI). The AlCl3-catalyzed reaction of (X) with (XI) also proceeds via bicyclo(2.2.2)octenes to yield 3-oxo-. alpha.-ionone (XIII). -(ITO, N.; ETOH, T.; J.
Oxidation of β,γ-Unsaturated Ketones with Molecular Oxygen Catalyzed by Metal Phthalocyanines and Porphyrins: A Practical Synthesis of Oxophorone.-A simple method for the oxidation of β-isophorone (III) to oxophorone (IV), an important key intermediate for the synthesis of carotenoids, is presented. This method can also be applied to the oxidation of acyclic unsaturated ketones (V). Compound (VIa) is an aggression controlling substance in bees.-(ITO, N.; ETOH, T.; HAGIWARA, H.; KATO, M.; Synthesis (1997) 2, 153-155; Res. Dev.
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